T3P-promoted synthesis of a series of novel 2-aryl-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones

Lee J. Silverberg, Carlos N. Pacheco, Debashish Sahu, Tapas Mal, Peter Scholl, Hany F. Sobhi, Heather G. Bradley, Omar A. Cardenas, Kyanna M. Gonzalez, Jasra M. Islam, Emily G. Kimmel, Winnie Li, Kristen C. Perhonitch, Jennifer T. Pothering, Michael E. Potts, Melissa E. Ramirez, Haley E. Reppert, Kelsey N. Shaffer

Research output: Contribution to journalArticle

Abstract

A series of twelve novel 2-aryl-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of C-aryl-N-phenyl imines with 3-mercaptopropionic acid. The reaction can also be run as a 3-component reaction, forming the imine in situ. The reactions were operationally simple, rapid and gave yields as high as 75%. This provides ready access to C-aryl-N-phenyl compounds in this family, which have been generally difficult to prepare.

Original languageEnglish (US)
Article number151836
JournalTetrahedron Letters
Volume61
Issue number18
DOIs
StatePublished - Apr 30 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Silverberg, L. J., Pacheco, C. N., Sahu, D., Mal, T., Scholl, P., Sobhi, H. F., Bradley, H. G., Cardenas, O. A., Gonzalez, K. M., Islam, J. M., Kimmel, E. G., Li, W., Perhonitch, K. C., Pothering, J. T., Potts, M. E., Ramirez, M. E., Reppert, H. E., & Shaffer, K. N. (2020). T3P-promoted synthesis of a series of novel 2-aryl-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones. Tetrahedron Letters, 61(18), [151836]. https://doi.org/10.1016/j.tetlet.2020.151836